I've only been to Chicago once.. and it was many years ago....

Where would you recommend that an enterprising lady stay if she were going to be in the city and available for 3-4 days?  

 
Downtown?  I know in many cities downtown is always met with resistance due to parking... but in many MAJOR cities, it isn't considered a dealbreaker.

O'hare?  I know airport areas are often popular with ladies who fly-- but I'm driving in so its not a draw for me unless its a draw for others..

Schaumburg?  

Any other areas of interest/ note?  

Oak Brook....centralized suburb and classy

yeah, they've only had one mall shooting this year.

There are lots of accommodations from which to choose (although depending on the choice, parking can still be a problem).  It is right off of the expressway and has an elevated train stop, making Schaumburg/Oak Brook/Downtown still only 15 minutes away.  It is convenient to any clients flying in/out of town.

For me personally, I’ll only see a visiting provider if she’s downtown. Just easier to get to than to schlep out to the burbs. But that’s just me.

Free parking in Oakbrook compared to Rosemont & Downtown and much less driving traffic.

When I visit I do the western burbs. Mostly Oakbrook. I don't do hotels much anymore but if need advice on vacation rentals to use let me know. Careful in Schaumburg as they do a lot of stings there for some reason. It's like the politic people have a chip on their shoulder.

I stay in  Schaumburg area it's very nice and easy to get around with Grate food ,if you need hotel info just ask

I would recommend splitting your time between both Downtown and the suburbs

 
Downtown
Downtown (has a rep for bad parking) but city guys understand there is a thing called parking garages and spothero to help with that. So i do recommend downtown because it is central and great for the men who live downtown, men getting off from work (yes some people still go into office) , and for you you can enjoy time in-between dates and enjoying the city a bit. (lakefront path, shopping on Michigan ave or maybe Oak street, starbucks reserve, Tavern etc)    

Suburbs  
Rosemont/Ohare, Schaumburg, Oakbrook, all great and around one another and the suburban men don't mind coming to either. Parking is ample, (ohare area charges for some hotels), easy to drive over to with little to no traffic. Hotels are beautiful and shopping is great in all areas. (Oakbrook shopping is better IMO)  

 
hope this helps,  
Mya

Many touring ladies tell me that Schaumburg and Oakbrook keep them the busiest